Bovine Metabolome Database: Showing metabocard for Normetanephrine (BMDB0000819)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:04 UTC

Update Date

2020-05-21 16:28:47 UTC

BMDB ID

BMDB0000819

Secondary Accession Numbers

BMDB00819

Metabolite Identification

Common Name

Normetanephrine

Description

Normetanephrine, also known as normetanephrine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Normetanephrine participates in a number of enzymatic reactions, within cattle. In particular, Normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In addition, Normetanephrine and pyrocatechol can be biosynthesized from norepinephrine and guaiacol through the action of the enzyme catechol O-methyltransferase. In cattle, normetanephrine is involved in the metabolic pathway called the tyrosine metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+/-)-normetanephrine	HMDB
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol	HMDB
3-Methoxy-noradrenaline	HMDB
3-O-Methyl-noradrenaline	HMDB
4-(2-Amino-1-hydroxyethyl)-2-methoxyphenol	HMDB
alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol	HMDB
DL-N-Normetanephrine	HMDB
DL-Normetanephrine	HMDB
L-Normetanephrine	HMDB
m-O-Methylnorepinephrine	HMDB
N111	HMDB
Normetadrenaline	HMDB
O-Methylnoradrenaline	HMDB
3 Methoxynoradrenaline	HMDB
3-Methoxynoradrenaline	HMDB

Chemical Formula

C₉H₁₃NO₃

Average Molecular Weight

183.2044

Monoisotopic Molecular Weight

183.089543287

IUPAC Name

4-(2-amino-1-hydroxyethyl)-2-methoxyphenol

Traditional Name

(+/-)-normetanephrine

CAS Registry Number

97-31-4

SMILES

COC1=CC(=CC=C1O)C(O)CN

InChI Identifier

InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3

InChI Key

YNYAYWLBAHXHLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
Secondary alcohol
1,2-aminoalcohol
Ether
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a guaiacol (CPD-11875 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	204 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.05	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.71	ALOGPS
logP	-0.39	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.94 m³·mol⁻¹	ChemAxon
Polarizability	19.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00di-2920000000-906a2c3ec3c929834c7b	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2920000000-906a2c3ec3c929834c7b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-df1660d54bc99d55b9bb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-1900000000-f8b939907bf23331b83f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-cb28fbf84eae6ad4628e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05e9-4900000000-65aa73bd819270237f34	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9200000000-de463de74a0d6a9bfdb1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9200000000-efafce5afe4a7c15067b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05ai-1900000000-93cae41cf9bbc8fb06fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4f226dd2298708c36b4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0h3s-5900000000-7420f0a05449387c69eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-fa66b6a75bb70a6e11cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05ai-1900000000-7eaa1d030beaeae5118f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-c2a7cb2d1889ec69b26a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9300000000-98a0488cc1211d99fa57	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-9997c3e9112e4558aa63	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-006t-0900000000-bd5a22c7a438d15be4bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-7900000000-863bf83793f05b65058a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-2a2538378e0bbcaed15f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-4414d75b49a2cc82bdb6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-b19888f59670d542cc35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-26872ea42b5102a407ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fdt-4900000000-2416e3adcd40b107923d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-f95a5de2b99b6807a9ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gx0-0900000000-e2ba422610b39356fe57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-3900000000-f9f0aaa8b3c0fcfee29a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-ec4dd90d9b4a388fca9c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2900000000-f0ee1c53996f65eaa5cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9300000000-91b1e27073d44d8f5025	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adrenal Gland
Adrenal Medulla
Brain
Platelet

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Medulla	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000819

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

46080

Wikipedia Link

Normetanephrine

METLIN ID

PubChem Compound

1237

PDB ID

Not Available

ChEBI ID

144308

References

Synthesis Reference

Sejbal, Jan; Krecek, Vaclav. Method of preparing normetanephrine. Czech. (1992), 4 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in catechol O-methyltransferase activity
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:: COMT
Uniprot ID:: A7MBI7
Molecular weight:: 30485.0

Reactions

Norepinephrine + Guaiacol → Normetanephrine + Pyrocatechol	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21398
Molecular weight:: 59758.0

Reactions

Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide	details

Showing metabocard for Normetanephrine (BMDB0000819)

Structure for BMDB0000819 (Normetanephrine)

Enzymes

Reactions

Reactions